escitalopram (CHEBI:36791)

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ChEBI Name	escitalopram

ChEBI ID	CHEBI:36791

Definition	A 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile that has S-configuration at the chiral centre. It is the active enantiomer of citalopram.

Stars	This entity has been manually annotated by the ChEBI Team.

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Formula

C20H21FN2O

Net Charge

Average Mass

324.39202

Monoisotopic Mass

324.16379

InChI

InChI=1S/C20H21FN2O/c1-23(2)11-3-10-20(17-5-7-18(21)8-6-17)19-9-4-15(13-22)12-16(19)14-24-20/h4-9,12H,3,10-11,14H2,1-2H3/t20-/m0/s1

InChIKey

WSEQXVZVJXJVFP-FQEVSTJZSA-N

SMILES

CN(C)CCC[C@]1(OCc2cc(ccc12)C#N)c1ccc(F)cc1

Metabolite of Species	Details
Homo sapiens (NCBI:txid9606)	Found in blood (UBERON:0000178). See: PubMed

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

Biological Role(s):	EC 3.4.21.26 (prolyl oligopeptidase) inhibitor Any EC 3.4.21.* (serine endopeptidase) inhibitor that interferes with the action of prolyl oligopeptidase (EC 3.4.21.26).

Application(s):	antidepressant Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions.

ChEBI Ontology
Outgoing	escitalopram (CHEBI:36791) has role antidepressant (CHEBI:35469) escitalopram (CHEBI:36791) has role EC 3.4.21.26 (prolyl oligopeptidase) inhibitor (CHEBI:76779) escitalopram (CHEBI:36791) is a 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile (CHEBI:77397) escitalopram (CHEBI:36791) is conjugate base of escitalopram(1+) (CHEBI:77406) escitalopram (CHEBI:36791) is enantiomer of (R)-citalopram (CHEBI:36792)

Incoming	citalopram (CHEBI:3723) has part escitalopram (CHEBI:36791) escitalopram(1+) (CHEBI:77406) is conjugate acid of escitalopram (CHEBI:36791) (R)-citalopram (CHEBI:36792) is enantiomer of escitalopram (CHEBI:36791)

IUPAC Name

(1S)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile

Brand Name	Source
Esertia	KEGG DRUG

Last Modified

09 October 2023